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T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

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Synonym(s):
7-Deazaadenosine
Empirical Formula (Hill Notation):
C11H14N4O4
CAS Number:
Molecular Weight:
266.25
Beilstein/REAXYS Number:
38498
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces tubercidicus

Quality Level

assay

~95%

form

powder

color

off-white

antibiotic activity spectrum

fungi
parasites
viruses

mode of action

DNA synthesis | interferes

SMILES string

O[C@H]1[C@@H](O)[C@H](N2C=CC3=C2N=CN=C3N)O[C@@H]1CO

InChI

1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1

InChI key

HDZZVAMISRMYHH-KCGFPETGSA-N

Gene Information

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This Item
S8559F7129N8028
Tubercidin from Streptomyces tubercidicus, ~95%

T0642

Tubercidin

Sinefungin 95% (HPLC), powder

S8559

Sinefungin

5-Fluorocytosine nucleoside analog

F7129

5-Fluorocytosine

antibiotic activity spectrum

fungi, viruses, parasites

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi

form

powder

form

powder

form

-

form

powder

assay

~95%

assay

95% (HPLC)

assay

≥99% (TLC)

assay

≥90% (HPLC)

biological source

Streptomyces tubercidicus

biological source

-

biological source

-

biological source

-

color

off-white

color

white to yellow

color

-

color

-

General description

Chemical structure: nucleoside

application

It is used to study tubercidin′s mechanism of toxicity, tubercidin resistance and is used as a selection agent. Tubercidin is used to study RNAi silencing. It is used to study the role of transmethylation in chemotaxis of eukaryotic cells.

Biochem/physiol Actions

Tubercidin is a toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. It inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata. Tubercidin inhibits glycolysis in Trypanosoma brucei. Tubercidin inhibits both chemotaxis and chemotaxis-dependent cell streaming of Dictyostelium, and chemotaxis of neutrophils at concentrations that have little effect on cell viability.
Toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. Mode of action: Inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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